GCLE Chemical Properties

Melting point:

153-155°C

Boiling point:

756.6±60.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

form 

Solid

pka

13.61±0.60(Predicted)

color 

White to Off-White

optical activity

Consistent with structure

InChIKey

KFCMZNUGNLCSJQ-NFBKMPQASA-N

SMILES

N12[C@@]([H])([C@H](NC(CC3=CC=CC=C3)=O)C1=O)SCC(CCl)=C2C(OCC1=CC=C(OC)C=C1)=O

CAS DataBase Reference

104146-10-3(CAS DataBase Reference)

Safety Information

RTECS 

XI0369883

HS Code 

2941.90.3000

GCLE Usage And Synthesis

Chemical Properties

White Solid

Uses

4-Methoxybenzyl 3-Chloromethyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate is a key intermediate of cephem compounds.

Uses

A key intermediate of cephem compounds.

Synthesis

The general procedure for the synthesis of (6R,7R)-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thiophene-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-4-methoxybenzyl ester, using the compound (CAS:131903-39-4) as a starting material, was as follows: in 2000 mL dioxane, 120 g of sodium bicarbonate ( 1.43 mol) and 200 g of azodioxanone sulfinic acid intermediate (0.336 mmol) and stirred at 10 to 15 °C. 30 g of chlorine gas (0.422 mol) was slowly passed for about 3 h. The reaction progress was monitored by HPLC until the peak area of the feedstock dropped below 0.5%. The passage of chlorine gas was stopped, sodium bicarbonate was removed by filtration and dioxane was recovered under vacuum. 2000 mL of methanol was added to dissolve the residue and the reaction temperature was maintained at 0-5 °C. Subsequently, a 900 mL methanol solution of 18 g sodium methanolate (0.34 mol) was added and the reaction was maintained at 0~5 °C for 30 min. The pH of the reaction system was adjusted to 4~6 with 10% hydrochloric acid and stirring was continued at 0~5°C for 1 hour. After completion of the reaction, the product was collected by filtration, washed with water and methanol sequentially, and dried to give 125 g of GCLE in 76.3% yield and ≥94% purity.

References

[1] Patent: CN107033162, 2017, A. Location in patent: Paragraph 0024; 0027

GCLE(104146-10-3)Related Product Information

• RESMETHRIN
• Acetylsalicylic acid
• Acetylcholine
• Acetylspiramycin
• Acetaminophen
• 4-Methoxybenzylchloride
• 7-Amino-3-cephem-4-carboxylic acid
• 7-Amino-3-methyl-3-cephem-4-carboxylic acid
• 3-Chloro-2-methylpropene
• 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid
• Methyl N,N-dimethylaminoacrylate
• Azetidine hydrochloride
• GLYCYLGLYCINE METHYL ESTER HYDROCHLORIDE
• GLYCYLGLYCINE ETHYL ESTER HYDROCHLORIDE
• Oxygen
• H-ALA-GLY-OME HCL
• H-SAR-OBZL HCL
• BUTTPARK 146\50-48